3-Aminolevamisole → 6-[m-(5-Methyl-1-phenylpyrazole-3-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

HRID 2166819ノート

反応式

HRID 2166819 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][N:14]3[C:10]([S:11][CH2:12][CH2:13]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C[Al](C)C.C([O:22][C:23]([C:25]1[CH:29]=[C:28]([CH3:30])[N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:26]=1)=O)C>ClCCl>[CH3:30][C:28]1[N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:26]=[C:25]([C:23]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]3[CH2:15][N:14]4[C:10]([S:11][CH2:12][CH2:13]4)=[N:9]3)[CH:5]=[CH:6][CH:7]=2)=[O:22])[CH:29]=1

参加物

5

反応物 3

HCID 30386693-AminolevamisoleHCID 10900438Ethyl 5-methyl-1-phenyl-1H-pyrazole-3-carboxylateHCID 16682925Trimethylaluminum

生成物 1

HCID 204979616-[m-(5-Methyl-1-phenylpyrazole-3-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (1.9 g, 8.7 mmol) in dry dichloromethane (40 ml) under nitrogen at room temperature was added trimethylaluminium (6 ml: 25% in hexane). After 20 min 5-methyl-1-phenylpyrazole 3-carboxylic acid ethyl ester (2 g, 8.7 mmol) in dry dichloromethane (5 ml) was added and the mixture heated under reflux for 3 days. The reaction was quenched by the slow addition of hydrochloric acid (20 ml, 2 N aqueous), basified with aqueous ammonia solution (5 N) and extracted with chloroform (3×200 ml). After drying the organic phase was concentrated in vacuo to afford an oil which was separated by column chromatography on alumina eluting with chloroform to afford the amide (2.41 g; 69%). Addition of isopropanolic hydrogen chloride gave the hydrochloride salt (1.56 g) recrystallised from ethanol.

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 3 days
  3. customThe reaction was quenched by the slow addition of hydrochloric acid (20 ml, 2 N aqueous)
  4. extractionextracted with chloroform (3×200 ml)
  5. customAfter drying the organic phase
  6. concentrationwas concentrated in vacuo
  7. customto afford an oil which
  8. customwas separated by column chromatography on alumina eluting with chloroform

出典と根拠

ORDレコード
ord-734027a5a4bd4fe0bc67026a03d15e8a
出典データセット
uspto-grants-1983_06
特許番号
US04389406

反応ノート

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